Formation of N-nitrosodimethylamine (NDMA) from dimethylamine during chlorination
- PMID:11878371
- DOI: 10.1021/es010684q
Formation of N-nitrosodimethylamine (NDMA) from dimethylamine during chlorination
Abstract
Chlorine disinfection of secondary wastewater effluent and drinking water can result in the production of the potent carcinogen N-nitrosodimethylamine (NDMA) at concentrations of approximately 100 and 10 parts per trillion (ng/L), respectively. Laboratory experiments with potential NDMA precursors indicate that NDMA formation can form during the chlorination of dimethylamine and other secondary amines. The formation of NDMA during chlorination may involve the slow formation of 1,1-dimethylhydrazine by the reaction of monochloramine and dimethylamine followed by its rapid oxidation to NDMA and other products including dimethylcyanamide and dimethylformamide. Other pathways also lead to NDMA formation during chlorination such as the reaction of sodium hypochlorite with dimethylamine. However, the rate of NDMA formation is approximately an order of magnitude slower than that observed when monochloramine reacts with dimethylamine. The reaction exhibits a strong pH dependence due to competing reactions. It may be possible to reduce NDMA formation during chlorination by removing ammonia prior to chlorination, by breakpoint chlorination, or by avoidance of the use of monochloramine for drinking water disinfection.
Similar articles
- Influence of the order of reagent addition on NDMA formation during chloramination.Schreiber IM, Mitch WA.Schreiber IM, et al.Environ Sci Technol. 2005 May 15;39(10):3811-8. doi: 10.1021/es0483286.Environ Sci Technol. 2005.PMID:15952390
- A kinetic model of N-nitrosodimethylamine (NDMA) formation during water chlorination/chloramination.Choi J, Valentine RL.Choi J, et al.Water Sci Technol. 2002;46(3):65-71.Water Sci Technol. 2002.PMID:12227605
- N-nitrosodimethylamine (NDMA) formation potential of amine-based water treatment polymers: Effects of in situ chloramination, breakpoint chlorination, and pre-oxidation.Park SH, Padhye LP, Wang P, Cho M, Kim JH, Huang CH.Park SH, et al.J Hazard Mater. 2015 Jan 23;282:133-40. doi: 10.1016/j.jhazmat.2014.07.044. Epub 2014 Jul 30.J Hazard Mater. 2015.PMID:25112551
- Occurrence, genotoxicity, and carcinogenicity of regulated and emerging disinfection by-products in drinking water: a review and roadmap for research.Richardson SD, Plewa MJ, Wagner ED, Schoeny R, Demarini DM.Richardson SD, et al.Mutat Res. 2007 Nov-Dec;636(1-3):178-242. doi: 10.1016/j.mrrev.2007.09.001. Epub 2007 Sep 12.Mutat Res. 2007.PMID:17980649Review.
- Precursors of nitrogenous disinfection by-products in drinking water--a critical review and analysis.Bond T, Templeton MR, Graham N.Bond T, et al.J Hazard Mater. 2012 Oct 15;235-236:1-16. doi: 10.1016/j.jhazmat.2012.07.017. Epub 2012 Jul 14.J Hazard Mater. 2012.PMID:22846217Review.
Cited by
- Pipe Dreams: Tapping into the Health Information in Our Sewers.Arnold C.Arnold C.Environ Health Perspect. 2016 May 1;124(5):A86-91. doi: 10.1289/ehp.124-A86.Environ Health Perspect. 2016.PMID:27135177Free PMC article.No abstract available.
- Role of Carbonyl Compounds forN-Nitrosamine Formation during Nitrosation: Kinetics and Mechanisms.Pan Y, Breider F, Barrios B, Minakata D, Deng H, von Gunten U.Pan Y, et al.Environ Sci Technol. 2024 Mar 12;58(10):4792-4801. doi: 10.1021/acs.est.3c07461. Epub 2024 Mar 1.Environ Sci Technol. 2024.PMID:38427382Free PMC article.
- Factors affectingN-nitrosodimethylamine formation from poly(diallyldimethyl-ammonium chloride) degradation during chloramination.Tan S, Jiang S, Li X, Yuan Q.Tan S, et al.R Soc Open Sci. 2018 Aug 8;5(8):180025. doi: 10.1098/rsos.180025. eCollection 2018 Aug.R Soc Open Sci. 2018.PMID:30225002Free PMC article.
- Metallocalix[4]arene Polymers for Gravimetric Detection ofN-Nitrosodialkylamines.Lu RQ, Yuan W, Croy RG, Essigmann JM, Swager TM.Lu RQ, et al.J Am Chem Soc. 2021 Dec 1;143(47):19809-19815. doi: 10.1021/jacs.1c08739. Epub 2021 Nov 18.J Am Chem Soc. 2021.PMID:34793165Free PMC article.
- An inducible propane monooxygenase is responsible for N-nitrosodimethylamine degradation by Rhodococcus sp. strain RHA1.Sharp JO, Sales CM, LeBlanc JC, Liu J, Wood TK, Eltis LD, Mohn WW, Alvarez-Cohen L.Sharp JO, et al.Appl Environ Microbiol. 2007 Nov;73(21):6930-8. doi: 10.1128/AEM.01697-07. Epub 2007 Sep 14.Appl Environ Microbiol. 2007.PMID:17873074Free PMC article.
Publication types
MeSH terms
Substances
Related information
LinkOut - more resources
Full Text Sources
Other Literature Sources
Research Materials
Miscellaneous